Holiday Homes in The Berkshires

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Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
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12 Dec - 14 Dec
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9 Jan - 11 Jan

Featured Holiday Homes in The Berkshires and around

Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"Nicole was phenomenal, the most speedy and responsive host I've had on any platform. The A-Frame was a perfect, cozy, and quaint little spot for our weekend getaway. It was clean and honestly portrayed in the photos. No complaints whatsoever. Thank you, Nicole!"
United States
James F.
The price is €334
includes taxes & fees
24 Nov - 25 Nov
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
TV
Florida Mountain Log Cabin

Florida Mountain Log Cabin

2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"We loved our 1 night stay here - it is a super cute log cabin with comfortable beds and very clean! Our favorite part was the fire pit for smores and the kids especially loved the cozy swings! Host was very accessible. Definitely recommend!"
United States
Kate R.
Florida Mountain Log Cabin
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is €345
includes taxes & fees
18 Nov - 19 Nov
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Exterior
North Getaway Cottage

North Getaway Cottage

Williamstown
9.4 out of 10, Exceptional, (23)
"The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. "
United States
Mary Alice H.
The price is €392
includes taxes & fees
17 Nov - 18 Nov
North Getaway Cottage
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
10.0 out of 10, Exceptional, (40)
"we had a wonderful time staying at the house, very comfortable and well equipped and responsive host."
United States
lisa s.
The price is €444
includes taxes & fees
15 Dec - 16 Dec
Cheerful 3-bedroom cottage with woodstove
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"We had a lovely one week stay at this property. The location was very convenient to all the restaurants and shops. The fall foliage was spectacular and truly enjoyed biking and hiking in the Berkshires."
United States
Farida K.
The price is €259
includes taxes & fees
17 Nov - 18 Nov
Home in Great Barrington
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock
9.8 out of 10, Exceptional, (72)
"Awesome place to stay to ski for the weekend. Skiing on and off was very easy, quick ride to dinner and plenty of room in the condo for everyone. Can’t wait to come back!"
United States
Christine L.
The price is €484
includes taxes & fees
16 Nov - 17 Nov
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is €214
includes taxes & fees
10 Dec - 11 Dec
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior
Bungalow in the Berkshires

Bungalow in the Berkshires

Lee
10.0 out of 10, Exceptional, (4)
"Great location, very clean and well appointed with everyth"
United States
Nick R.
The price is €339
includes taxes & fees
30 Nov - 1 Dec
Bungalow in the Berkshires
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Family ski trip was made extremely enjoyable by staying at this property. Everything worked out as advertised"
United States
Henry C.
The price is €648
includes taxes & fees
8 Dec - 9 Dec
Comfortable Berkshires retreat on mtn resort, SISO
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Great Barrington Get Away

Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is €459
includes taxes & fees
16 Nov - 17 Nov
Great Barrington Get Away
Fridge, microwave, oven, stovetop
The Greylock Cabin

The Greylock Cabin

Florida
10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay at Greylock Cabin! It is clean, well maintained, and was very prepared for our arrival. Extra towels, bedding, and basic cookware were helpful for a comfortable getaway. It was easy to access the cabin and park. The host was very communicative and easy to reach throughout our stay. The outdoor space had a great view and was perfect to grill and unwind by the fire."
United States
Robert G.
The price is €383
includes taxes & fees
11 Dec - 12 Dec
The Greylock Cabin
Games room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.0 out of 10, Wonderful, (4)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is €263
includes taxes & fees
17 Nov - 18 Nov
Pet Friendly Riverfront Home in Great Barrington
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington
The price is €505
includes taxes & fees
19 Nov - 20 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is €433
includes taxes & fees
16 Nov - 17 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
United States
Jim O.
The price is €981
includes taxes & fees
18 Nov - 19 Nov
Hancock Village Inn Near Jiminy Peak
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington
10.0 out of 10, Exceptional, (1)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is €1,179
includes taxes & fees
15 Nov - 16 Nov
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is €656
includes taxes & fees
21 Nov - 22 Nov
Spacious 5-bedroom house in charming Lee with WiFi
Property grounds
The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.

Easthampton Ma.
10.0 out of 10, Exceptional, (70)
"A very short but a really fun stay. Great location to just relax and get away from it all."
United States
Naseem P.
The price is €238
includes taxes & fees
8 Dec - 9 Dec
The Creation Station is a cozy place so make yourself at home.
Interior
Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

Greenfield
10.0 out of 10, Exceptional, (44)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
United States
Shanyn
The price is €177
includes taxes & fees
17 Nov - 18 Nov
Lovely 2nd Floor Apartment
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top The Berkshires Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"The room was wonderful, specious, clean and great bathroom!"
Israel 2-night trip
Posted 5 days ago
Hotel On North

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